Licoricidin (BioDeep_00000270201)

 

Secondary id: BioDeep_00000000917

natural product PANOMIX_OTCML-2023


代谢物信息卡片


4- [ (3R) -7-Hydroxy-5-methoxy-6- (3-methylbut-2-enyl) -3,4-dihydro-2H-chromen-3-yl] -2- (3-methylbut-2-enyl) benzene-1,3-diol

化学式: C26H32O5 (424.225)
中文名称: 甘草西定, 甘草定
谱图信息: 最多检出来源 Viridiplantae(plant) 12.54%

分子结构信息

SMILES: C(C)(C)=CCc(c3OC)c(O)c(C1)c(c3)OCC(c(c2)c(c(c(c2)O)C=CC(C)C)O)1
InChI: InChI=1S/C26H32O5/c1-15(2)6-8-19-22(27)11-10-18(25(19)28)17-12-21-24(31-14-17)13-23(30-5)20(26(21)29)9-7-16(3)4/h6-8,10-11,13,15,17,27-29H,9,12,14H2,1-5H3/b8-6+

描述信息

Licoricidin is a member of the class of hydroxyisoflavans that is R-isoflavan with hydroxy groups at positions 7, 2 and 4, a methoxy group at position 5 and prenyl groups at positions 6 and 3. Isolated from Glycyrrhiza uralensis, it exhibits antibacterial activity. It has a role as an antibacterial agent and a plant metabolite. It is a member of hydroxyisoflavans, an aromatic ether and a methoxyisoflavan.
Licoricidin is a natural product found in Glycyrrhiza, Glycyrrhiza glabra, and other organisms with data available.
See also: Glycyrrhiza uralensis Root (part of).
A member of the class of hydroxyisoflavans that is R-isoflavan with hydroxy groups at positions 7, 2 and 4, a methoxy group at position 5 and prenyl groups at positions 6 and 3. Isolated from Glycyrrhiza uralensis, it exhibits antibacterial activity.

同义名列表

23 个代谢物同义名

1,3-BENZENEDIOL, 4-((3R)-3,4-DIHYDRO-7-HYDROXY-5-METHOXY-6-(3-METHYL-2-BUTENYL)-2H-1-BENZOPYRAN-3-YL)-2-(3-METHYL-2-BUTENYL)-; 4-[(3r)-7-hydroxy-5-methoxy-6-(3-methylbut-2-en-1-yl)-3,4-dihydro-2h-chromen-3-yl]-2-(3-methylbut-2-en-1-yl)benzene-1,3-diol; 4-((3R)-7-hydroxy-5-methoxy-6-(3-methylbut-2-en-1-yl)-3,4-dihydro-2H-chromen-3-yl)-2-(3-methylbut-2-en-1-yl)benzene-1,3-diol; 4-[7-Hydroxy-5-methoxy-6-(3-methylbut-2-en-1-yl)-3,4-dihydro-2H-1-benzopyran-3-yl]-2-(3-methylbut-2-en-1-yl)benzene-1,3-diol; 4-[(3R)-7-hydroxy-5-methoxy-6-(3-methylbut-2-enyl)-3,4-dihydro-2H-chromen-3-yl]-2-(3-methylbut-2-enyl)benzene-1,3-diol; 4-[(R)-7-Hydroxy-5-methoxy-6-(3-methyl-but-2-enyl)-1-benzopyran-3-yl]-2-((E)-3-methyl-but-2-enyl)-benzene-1,3-diol; 4-((R)-7-Hydroxy-5-methoxy-6-(3-methyl-but-2-enyl)-1-benzopyran-3-yl)-2-((E)-3-methyl-but-2-enyl)-benzene-1,3-diol; 4-[7-Hydroxy-5-methoxy-6-(3-methylbut-2-enyl)-3,4-dihydro-2H-chromen-3-yl]-2-(3-methylbut-2-enyl)benzene-1,3-diol; (R)-4-(7-hydroxy-5-methoxy-6-(3-methylbut-2-en-1-yl)chroman-3-yl)-2-(3-methylbut-2-en-1-yl)benzene-1,3-diol; 4-[(3R)-7-hydroxy-5-methoxy-6-(3-methylbut-2-enyl)chroman-3-yl]-2-(3-methylbut-2-enyl)benzene-1,3-diol; 2,4,7-trihydroxy-5-methoxy-3,6-diisopentenyl-isoflavan; 7-O-DEMETHYLLICORISOFLAVAN A; LICORISOFLAVAN B; (+)-LICORICIDIN; Licoricidin; 4-[(3R)-7-hydroxy-5-methoxy-6-(3-methylbut-2-enyl)-3-chromanyl]-2-(3-methylbut-2-enyl)benzene-1,3-diol; 4-[(3R)-7-hydroxy-5-methoxy-6-(3-methylbut-2-enyl)chroman-3-yl]-2-(3-methylbut-2-enyl)resorcinol; AIDS-096021; AIDS096021; 30508-27-1; 5,2,4-Trihydroxy-7-methoxy-6,3-diprenylisoflavan; 4- [ (3R) -7-Hydroxy-5-methoxy-6- (3-methylbut-2-enyl) -3,4-dihydro-2H-chromen-3-yl] -2- (3-methylbut-2-enyl) benzene-1,3-diol; Licoricidin



数据库引用编号

38 个数据库交叉引用编号

分类词条

相关代谢途径

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代谢反应

0 个相关的代谢反应过程信息。

Reactome(0)

BioCyc(0)

WikiPathways(0)

Plant Reactome(0)

INOH(0)

PlantCyc(0)

COVID-19 Disease Map(0)

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PharmGKB(0)

36 个相关的物种来源信息

在这里通过桑基图来展示出与当前的这个代谢物在我们的BioDeep知识库中具有相关联信息的其他代谢物。在这里进行关联的信息来源主要有：

  • PubMed: 来源于PubMed文献库中的文献信息，我们通过自然语言数据挖掘得到的在同一篇文献中被同时提及的相关代谢物列表，这个列表按照代谢物同时出现的文献数量降序排序，取前10个代谢物作为相关研究中关联性很高的代谢物集合展示在桑基图中。
  • NCBI Taxonomy: 通过文献数据挖掘，得到的代谢物物种来源信息关联。这个关联信息同样按照出现的次数降序排序，取前10个代谢物作为高关联度的代谢物集合展示在桑吉图上。
  • Chemical Taxonomy: 在物质分类上处于同一个分类集合中的其他代谢物
  • Chemical Reaction: 在化学反应过程中，存在为当前代谢物相关联的生化反应过程中的反应底物或者反应产物的关联代谢物信息。

点击图上的相关代谢物的名称，可以跳转到相关代谢物的信息页面。

亚细胞结构定位 关联基因列表
Cytoplasm 11 BCL2, CALR, CASP3, CASP9, CTNNB1, CYP2C19, CYP2C9, CYP3A4, HMGB1, PTPN1, VEGFA
Peripheral membrane protein 2 HMGB1, PTPN1
Endoplasmic reticulum membrane 10 BCL2, CALR, CYP2C19, CYP2C9, CYP3A4, HSP90B1, ICMT, PTPN1, UGT1A8, UGT1A9
Nucleus 9 BCL2, CALR, CASP3, CASP9, CTNNB1, HMGB1, HSP90B1, JUN, VEGFA
cytosol 8 BCL2, CALR, CASP3, CASP9, CTNNB1, HSP90B1, LCK, PTPN1
centrosome 1 CTNNB1
nucleoplasm 4 CASP3, CTNNB1, HMGB1, JUN
RNA polymerase II transcription regulator complex 1 JUN
Cell membrane 4 ADRB3, CTNNB1, HMGB1, LCK
Lipid-anchor 1 LCK
Cytoplasmic side 2 LCK, PTPN1
lamellipodium 1 CTNNB1
Multi-pass membrane protein 3 ADRB3, ICMT, UCP1
Synapse 1 CTNNB1
cell cortex 1 CTNNB1
cell junction 1 CTNNB1
cell surface 3 CALR, HMGB1, VEGFA
glutamatergic synapse 4 CALR, CASP3, CTNNB1, PTPN1
Golgi apparatus 1 VEGFA
mitochondrial inner membrane 1 UCP1
neuronal cell body 1 CASP3
postsynapse 2 CALR, PTPN1
presynaptic membrane 1 CTNNB1
smooth endoplasmic reticulum 2 CALR, HSP90B1
Cytoplasm, cytosol 2 CALR, LCK
acrosomal vesicle 1 CALR
endosome 1 HMGB1
plasma membrane 7 ADRB3, CTNNB1, CYP2C19, CYP2C9, HMGB1, LCK, TPSG1
Membrane 11 BCL2, CALR, CTNNB1, CYP3A4, HSP90B1, ICMT, PTPN1, TPSG1, UGT1A8, UGT1A9, VEGFA
basolateral plasma membrane 1 CTNNB1
extracellular exosome 4 CALR, CTNNB1, HSP90B1, LCK
endoplasmic reticulum 9 BCL2, CALR, HMGB1, HSP90B1, ICMT, PTPN1, UGT1A8, UGT1A9, VEGFA
extracellular space 4 CALR, HMGB1, TPSG1, VEGFA
perinuclear region of cytoplasm 3 CALR, CTNNB1, HSP90B1
Schaffer collateral - CA1 synapse 1 CTNNB1
adherens junction 2 CTNNB1, VEGFA
apicolateral plasma membrane 1 CTNNB1
bicellular tight junction 1 CTNNB1
mitochondrion 3 BCL2, CASP9, UCP1
protein-containing complex 5 BCL2, CASP9, CTNNB1, HSP90B1, PTPN1
intracellular membrane-bounded organelle 3 CYP2C19, CYP2C9, CYP3A4
Microsome membrane 2 CYP2C9, CYP3A4
postsynaptic density 1 CASP3
Secreted 2 HMGB1, VEGFA
extracellular region 4 CALR, HMGB1, HSP90B1, VEGFA
Mitochondrion outer membrane 1 BCL2
Single-pass membrane protein 4 BCL2, TPSG1, UGT1A8, UGT1A9
mitochondrial outer membrane 1 BCL2
mitochondrial matrix 1 PTPN1
Extracellular side 1 HMGB1
transcription regulator complex 2 CTNNB1, JUN
Nucleus membrane 1 BCL2
Bcl-2 family protein complex 1 BCL2
nuclear membrane 1 BCL2
external side of plasma membrane 1 CALR
Secreted, extracellular space, extracellular matrix 2 CALR, VEGFA
Z disc 1 CTNNB1
beta-catenin destruction complex 1 CTNNB1
Wnt signalosome 1 CTNNB1
midbody 1 HSP90B1
Early endosome 1 PTPN1
apical part of cell 1 CTNNB1
cell-cell junction 1 CTNNB1
postsynaptic membrane 1 CTNNB1
Mitochondrion inner membrane 1 UCP1
Membrane raft 1 LCK
pore complex 1 BCL2
Cytoplasm, cytoskeleton 1 CTNNB1
focal adhesion 3 CALR, CTNNB1, HSP90B1
Cell junction, adherens junction 1 CTNNB1
flotillin complex 1 CTNNB1
extracellular matrix 1 VEGFA
collagen-containing extracellular matrix 2 CALR, HSP90B1
secretory granule 1 VEGFA
fascia adherens 1 CTNNB1
lateral plasma membrane 1 CTNNB1
receptor complex 1 ADRB3
chromatin 1 JUN
phagocytic vesicle membrane 1 CALR
cell periphery 1 CTNNB1
Chromosome 1 HMGB1
Cytoplasm, cytoskeleton, cilium basal body 1 CTNNB1
mitochondrial crista 1 PTPN1
spindle pole 1 CTNNB1
nuclear chromosome 1 JUN
postsynaptic density, intracellular component 1 CTNNB1
microvillus membrane 1 CTNNB1
nuclear envelope 1 CALR
Endomembrane system 2 CTNNB1, PTPN1
endosome lumen 1 PTPN1
sorting endosome 1 PTPN1
Melanosome 1 HSP90B1
euchromatin 2 CTNNB1, JUN
myelin sheath 1 BCL2
sperm plasma membrane 1 HSP90B1
ficolin-1-rich granule lumen 1 HMGB1
secretory granule lumen 1 HMGB1
endoplasmic reticulum quality control compartment 1 CALR
endoplasmic reticulum lumen 2 CALR, HSP90B1
transcription repressor complex 1 HMGB1
platelet alpha granule lumen 1 VEGFA
beta-catenin-TCF complex 1 CTNNB1
Endoplasmic reticulum-Golgi intermediate compartment membrane 1 CALR
immunological synapse 1 LCK
apoptosome 1 CASP9
presynaptic active zone cytoplasmic component 1 CTNNB1
Sarcoplasmic reticulum lumen 2 CALR, HSP90B1
endoplasmic reticulum-Golgi intermediate compartment 1 HMGB1
protein-DNA complex 1 CTNNB1
death-inducing signaling complex 1 CASP3
lumenal side of endoplasmic reticulum membrane 1 CALR
MHC class I peptide loading complex 1 CALR
pericentriolar material 1 LCK
condensed chromosome 1 HMGB1
catenin complex 1 CTNNB1
endocytic vesicle lumen 2 CALR, HSP90B1
ribosome 1 CALR
transcription factor AP-1 complex 1 JUN
alphav-beta3 integrin-HMGB1 complex 1 HMGB1
endoplasmic reticulum chaperone complex 1 HSP90B1
Cytoplasmic vesicle, secretory vesicle, Cortical granule 1 CALR
cortical granule 1 CALR
Cytolytic granule 1 CALR
BAD-BCL-2 complex 1 BCL2
[N-VEGF]: Cytoplasm 1 VEGFA
[VEGFA]: Secreted 1 VEGFA
[Isoform L-VEGF189]: Endoplasmic reticulum 1 VEGFA
[Isoform VEGF121]: Secreted 1 VEGFA
[Isoform VEGF165]: Secreted 1 VEGFA
VEGF-A complex 1 VEGFA
beta-catenin-TCF7L2 complex 1 CTNNB1
cytoplasmic side of endoplasmic reticulum membrane 1 PTPN1
beta-catenin-ICAT complex 1 CTNNB1
Scrib-APC-beta-catenin complex 1 CTNNB1
caspase complex 1 CASP9


文献列表

  • Pei-Ju Wu, Hui-Ling Chiou, Yi-Hsien Hsieh, Chia-Liang Lin, Hsiang-Lin Lee, I-Chun Liu, Tsung-Ho Ying. Induction of immunogenic cell death effect of licoricidin in cervical cancer cells by enhancing endoplasmic reticulum stress-mediated high mobility group box 1 expression. Environmental toxicology. 2023 Apr; ?(?):. doi: 10.1002/tox.23793. [PMID: 37013980]
  • Hyun-Su Lee, Jooyoung Kim, Hyun Gyu Choi, Eun-Kyung Kim, Chang-Duk Jun. Licoricidin Abrogates T-Cell Activation by Modulating PTPN1 Activity and Attenuates Atopic Dermatitis In Vivo. The Journal of investigative dermatology. 2021 10; 141(10):2490-2498.e6. doi: 10.1016/j.jid.2021.02.759. [PMID: 33857487]
  • Jing-Ran Fan, Yi Kuang, Ze-Yuan Dong, Yang Yi, Yan-Xia Zhou, Bin Li, Xue Qiao, Min Ye. Prenylated Phenolic Compounds from the Aerial Parts of Glycyrrhiza uralensis as PTP1B and α-Glucosidase Inhibitors. Journal of natural products. 2020 04; 83(4):814-824. doi: 10.1021/acs.jnatprod.9b00262. [PMID: 32196343]
  • Pil Joung Cho, Ju-Hyun Kim, Hye Suk Lee, Jeong Ah Kim, Sangkyu Lee. Identification of specific UGT1A9-mediated glucuronidation of licoricidin in human liver microsomes. Biopharmaceutics & drug disposition. 2019 Feb; 40(2):94-98. doi: 10.1002/bdd.2169. [PMID: 30636046]
  • So Young Park, Soo Jin Kwon, Soon Sung Lim, Jin-Kyu Kim, Ki Won Lee, Jung Han Yoon Park. Licoricidin, an Active Compound in the Hexane/Ethanol Extract of Glycyrrhiza uralensis, Inhibits Lung Metastasis of 4T1 Murine Mammary Carcinoma Cells. International journal of molecular sciences. 2016 Jun; 17(6):. doi: 10.3390/ijms17060934. [PMID: 27314329]
  • Shuai Ji, Ziwei Li, Wei Song, Yongrui Wang, Wenfei Liang, Kai Li, Shunan Tang, Qi Wang, Xue Qiao, Demin Zhou, Siwang Yu, Min Ye. Bioactive Constituents of Glycyrrhiza uralensis (Licorice): Discovery of the Effective Components of a Traditional Herbal Medicine. Journal of natural products. 2016 Feb; 79(2):281-92. doi: 10.1021/acs.jnatprod.5b00877. [PMID: 26841168]
  • Jacquelyn R Villinski, Chantal Bergeron, Joseph C Cannistra, James B Gloer, Christina M Coleman, Daneel Ferreira, Jabrane Azelmat, Daniel Grenier, Stefan Gafner. Pyrano-isoflavans from Glycyrrhiza uralensis with antibacterial activity against Streptococcus mutans and Porphyromonas gingivalis. Journal of natural products. 2014 Mar; 77(3):521-6. doi: 10.1021/np400788r. [PMID: 24479468]
  • C Messier, F Epifano, S Genovese, D Grenier. Licorice and its potential beneficial effects in common oro-dental diseases. Oral diseases. 2012 Jan; 18(1):32-9. doi: 10.1111/j.1601-0825.2011.01842.x. [PMID: 21851508]
  • Vu Dang La, Shin-ichi Tanabe, Chantal Bergeron, Stefan Gafner, Daniel Grenier. Modulation of matrix metalloproteinase and cytokine production by licorice isolates licoricidin and licorisoflavan A: potential therapeutic approach for periodontitis. Journal of periodontology. 2011 Jan; 82(1):122-8. doi: 10.1902/jop.2010.100342. [PMID: 20722535]
  • So Young Park, Soon Sung Lim, Jin Kyu Kim, Il-Jun Kang, Jong-Sang Kim, Choonghwan Lee, Jongdai Kim, Jung Han Yoon Park. Hexane-ethanol extract of Glycyrrhiza uralensis containing licoricidin inhibits the metastatic capacity of DU145 human prostate cancer cells. The British journal of nutrition. 2010 Nov; 104(9):1272-82. doi: 10.1017/s0007114510002114. [PMID: 20487583]
  • Toshio Fukai, Kazue Satoh, Taro Nomura, Hiroshi Sakagami. Antinephritis and radical scavenging activity of prenylflavonoids. Fitoterapia. 2003 Dec; 74(7-8):720-4. doi: 10.1016/j.fitote.2003.07.004. [PMID: 14630182]
  • Toshio Fukai, Ai Marumo, Kiyoshi Kaitou, Toshihisa Kanda, Sumio Terada, Taro Nomura. Anti-Helicobacter pylori flavonoids from licorice extract. Life sciences. 2002 Aug; 71(12):1449-63. doi: 10.1016/s0024-3205(02)01864-7. [PMID: 12127165]
  • Y Tanaka, H Kikuzaki, S Fukuda, N Nakatani. Antibacterial compounds of licorice against upper airway respiratory tract pathogens. Journal of nutritional science and vitaminology. 2001 Jun; 47(3):270-3. doi: 10.3177/jnsv.47.270. [PMID: 11575586]
  • S Nagumo, A Fukuju, M Takayama, M Nagai, R Yanoshita, Y Samejima. Inhibition of lysoPAF acetyltransferase activity by components of licorice root. Biological & pharmaceutical bulletin. 1999 Oct; 22(10):1144-6. doi: 10.1248/bpb.22.1144. [PMID: 10549875]